HS-cellulose sulfate catalyzed synthesis of dihydroquinazolinones derivatives in water.
Entrya | R1 | R2 | Pro | Time (h) | Yieldb (%) |
---|---|---|---|---|---|
1 | –C6H5 | H | 3a | 0.7 | 94 (90, 88, 82)c |
2 | 4-CH3–C6H4 | H | 3b | 1.5 | 87 |
3d | 4-N(CH3)2–C6H4 | H | 3c | 1.5 | 98 |
4 | 4-OCH3–C6H4 | H | 3d | 1.0 | 86 |
5 | 4-NO2–C6H4 | H | 3e | 1.0 | 87 |
6 | 4-COOH–C6H4 | H | 3f | 2.0 | 91 |
7d | 4-C6H5–C6H4 | H | 3g | 2.0 | 80 |
8 | 4-F–C6H4 | H | 3h | 1.0 | 89 |
9d | 4-Br–C6H4 | H | 3i | 1.5 | 85 |
10d | 4-Cl–C6H4 | H | 3j | 1.5 | 92 |
11 | 2-Cl–C6H4 | H | 3k | 2.0 | 98 |
12 | 3-Cl–C6H4 | H | 3l | 2.0 | 83 |
13 | 4-OH–3-OCH3–C6H4 | H | 3m | 1.0 | 95 |
14 | –C4H3S | H | 3n | 2.0 | 88 |
15 | –C6H5 | 4-NO2 | 3o | 1.5 | 91 |
16 | 4-CH3–C6H5 | 4-NO2 | 3p | 1.5 | 90 |
17 | 4-Cl–C6H5 | 4-NO2 | 3q | 1.5 | 89 |
18 | 2-Cl–C6H5 | 4-NO2 | 3r | 2.0 | 92 |
19 | –C6H5 | 5-Cl | 3s | 6.0 | N.R |
20 | –C6H5 | 5-OCH3 | 3t | 6.0 | Trace |
Reaction conditions: aromatic aldehyde (0.5 mmol), aminobenzamide (0.5 mmol), HS-cellulose sulphate (10 mg), 60 °C; water (1.5 mL). The reactions were run until completion as indicated by TLC. N.R: no reaction. All the compounds are known, characterized by 1H NMR and 13C NMR.
Isolated yield.
The recovered catalyst cycle yield.
The solvent was water : ethanol = 1 : 1.